Iloprost - Moligand™, 10 mM in DMSO , CAS No.78919-13-8

CAS: 78919-13-8 Cat. No.: I1499272 Summenformel: C₂₂H₃₂O₄ Molekulargewicht: 360.49 EG-Nummer: 636-055-8

GRADE & PURITY Moligand™, 10 mM in DMSO

Storage

Store at -80°C

Shipped In

Dry ice packs + Cold packs

Übersicht

Iloprost (ZK 36374; Ciloprost) is a prostacyclin (PGI2) analogue, involves in embryo development and inflammation improvement, and inhibits tumor metastasis. Iloprost can be used for peripheral vascular research .

Specifications

Spezifikationen & Reinheit

Moligand™, 10 mM in DMSO

Storage

Store at -80°C

Verschickt in

Dry ice packs + Cold packs

Dieses Produkt erfordert Kühlkettenversand. Grundversand und andere Economy-Optionen sind nicht verfügbar.

Note

Moligand™

Namen und Kennungen

• Isomere SMILES: CC#CCC(C)[C@@H](/C=C/[C@H]1[C@@H](C[C@H]2[C@@H]1C/C(=C/CCCC(=O)O)/C2)O)O
• Molekulargewicht: 360.49
• Reaxy-Rn: 7222687
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=7222687&ln=

Application Protocols

No tested application protocols are provided in the Product Data for this item. The following are general, literature-based starting points for small-molecule ligands like iloprost and should be optimized by the user.

• Stock preparation:

  • Dissolve in anhydrous DMSO or ethanol to 1–10 mM. Vortex gently and protect from light. Filter through 0.2 µm PTFE if particulate is observed.
  • Aliquot into low-bind microtubes; store at −80°C. Avoid repeated freeze–thaw.

• Cellular assay dosing:

  • Dilute stock into pre-warmed assay buffer or medium to achieve final concentrations spanning ≥8-point half-log or quarter-log serial dilutions.
  • Keep final vehicle ≤0.1–0.5% v/v as assay allows. Include matched vehicle controls.

• cAMP accumulation assay (IP receptor readout, general):

  • Plate IP-expressing cells, equilibrate, then treat with iloprost dilutions for 10–30 min at 37°C.
  • Detect cAMP via HTRF/EIA kits per manufacturer’s instructions.

• LC–MS reference standard use:

  • Prepare calibration levels in 50:50 water:acetonitrile containing 0.1% formic acid (or appropriate buffer) immediately before analysis.
  • Store working solutions on ice and protected from light; discard after session to avoid degradation.

Note: These are general guidelines and not validated for this specific SKU. Always verify suitability for your system.

Biological Roles

General/literature context (no therapeutic claims; for research background):

• Class: Iloprost is a synthetic analog of prostacyclin (PGI2), a member of the eicosanoid family derived from arachidonic acid metabolism via the cyclooxygenase and prostacyclin synthase pathway.
• Primary target: Prostacyclin (IP, PTGIR) receptor, a G protein–coupled receptor. IP activation typically couples to Gs, elevating intracellular cAMP and modulating downstream kinases and transcriptional programs.
• Functional themes studied in vitro: Vascular signaling, platelet function pathways, and endothelial biology. Iloprost serves as a stable, selective tool to probe IP receptor biology relative to endogenous PGI2, which is chemically labile.
• Selectivity considerations: At high concentrations, some prostanoid analogs may show cross-reactivity at other prostanoid receptors (EP/DP) depending on system context; careful titration and counter-screening are recommended.
• Cellular handling: Due to lipophilicity and acid functionality, partitioning into membranes and nonspecific binding can influence apparent potency; assay design should consider carrier proteins, albumin, or defined lipid content.

Note: This tab provides biological background to aid experimental design only. For this specific item, no target-specific validation data are provided in the Product Data.

Buffer Applications

Iloprost is not a buffering reagent and is not typically used to prepare buffer systems.

Practical notes for assay buffers (general guidance):

• Use standard physiological buffers (e.g., HEPES, PBS) and add iloprost from a concentrated DMSO or ethanol stock to achieve the desired final concentration while keeping the organic vehicle low (≤0.1–1% v/v, as assay permits).
• Consider inclusion of carrier proteins (e.g., 0.1–0.5% fatty acid–free BSA) or 0.01–0.05% nonionic surfactant to mitigate adsorption and improve delivery at low nanomolar concentrations.
• Maintain controlled pH (typically 7.2–7.4 for mammalian cell assays) to ensure consistent ionization of the carboxylate group across replicates.

Green Alternatives

Although iloprost itself is the analyte/ligand (not a process solvent), greener choices can be made for its dissolution and handling.

Greener solvent considerations (general/literature guidance):

• Prefer ethanol/water co-solvent systems over halogenated or high-toxicity solvents where assay-compatible.
• Replace DMF/MeCN in sample prep with ethanol or isopropanol when chromatographic method tolerates.
• Employ cyclodextrin complexation or small amounts of nonionic surfactant to enable aqueous formulations, reducing DMSO content.

Comparison (general):

• DMSO vs ethanol:
  • DMSO: High solubilizing power; low volatility; biodegradable but may have aquatic toxicity concerns at scale; typically used at ≤1% in assays.
  • Ethanol: Renewable, low toxicity, rapidly biodegradable; volatility can aid solvent removal but may complicate assay handling.
• Aqueous buffer with solubilizer: Minimizes organic solvent use; may improve biocompatibility; requires optimization to prevent precipitation/adsorption.

Operational practices:

• Use amber glass vials to extend solution life and minimize repeats.
• Prepare minimal-volume, on-demand stocks to reduce waste.
• Adopt microscale assay formats (low volume plates) to reduce solvent consumption.

Pharmaceutical Uses

No clinical or therapeutic claims are made for this catalog item. For research use only.

Research/manufacturing context (general/literature information):

• Reference standard: Iloprost is commonly used as a reference standard in analytical method development and validation (e.g., LC–UV/LC–MS) for prostacyclin-class compounds.
• Formulation research: Serves as a model prostanoid for studying excipient effects on solubility, stability (light/oxidation), and delivery from solvent systems or polymeric matrices in preclinical formulation experiments.
• Impurity profiling: Useful for system suitability and retention-time locking when profiling prostanoid-related impurities or degradation products.

Regulatory/compendial status: Not specified for this item; refer to CoA/Spec Sheet and applicable pharmacopeial references if required for your workflow.

Physical Properties

Item-specific physicochemical values are not provided in the Product Data for this listing.

• Appearance: Not specified for this item; refer to CoA/Spec Sheet.
• Molecular weight: Not specified for this item; refer to CoA/Spec Sheet.
• Melting point, boiling point, density, refractive index: Not specified for this item; refer to CoA/Spec Sheet.
• Aqueous solubility: Not specified for this item; refer to CoA/Spec Sheet.

General/literature guidance for prostacyclin analogs (for planning only; not item specifications):

• Solubility profile: Typically sparingly soluble in water at neutral pH due to a largely lipophilic backbone; improved solubility in polar aprotic solvents (e.g., DMSO) and lower alcohols (e.g., ethanol). Aqueous solubility often increases in basic media (carboxylate formation) or with co-solvents/surfactants.
• Ionization: Contains a carboxylic acid group (weak acid); pKa for prostanoid carboxylates commonly ~4–5 (literature, compound-class estimate; exact value for iloprost not specified here).
• Partitioning: Amphiphilic with a tendency to adsorb to plastic surfaces at low concentrations; use low-bind plastics or glass when handling dilute solutions.
• Stability considerations: Like many eicosanoid analogs, iloprost can be sensitive to light, oxygen, and elevated temperature; plan to minimize exposure during handling and storage (see Storage & Reconstitution).

Quality and Grades

• Grade/Purity: Moligand™ (as provided in Product Data)

What Moligand™ typically implies (general description; not item-specific specifications):

• Intended for small-molecule screening, target validation, and SAR workflows where reliable identity and purity are critical for reproducible bioassay results.
• Common quality controls for such grades include structure confirmation by NMR and/or HRMS and purity assessment by LC/UV or LC–MS. Specific acceptance criteria (e.g., % purity, water or residual solvents) are Not specified for this item; refer to CoA/Spec Sheet.
• Packaging often optimized for high-throughput screening (HTS), with small aliquots to minimize freeze–thaw cycles and adsorption losses (packaging details not specified for this item).

Stabilizers/impurities:

• Stabilizers, counter-ions, and salt form are Not specified for this item; refer to CoA/Spec Sheet.

How to use this grade effectively:

• Verify identity/purity upon receipt if your workflow demands traceable qualification (e.g., orthogonal LC method, qNMR).
• For screening, prepare a concentrated DMSO or ethanol stock under low-light conditions; aliquot into low-bind vials/plates to improve dose–response accuracy.

Reaction and Applications

This product is supplied as a research ligand/compound for discovery and screening rather than as a synthetic reagent. Accordingly, “reactions” here refer to experimental applications in chemical biology and pharmacology.

Research applications (general/literature context; not item-specific claims):

• GPCR ligand studies: Iloprost is widely used as a reference agonist for the prostacyclin (IP) receptor in binding assays, cAMP accumulation readouts, reporter assays, and pathway deconvolution experiments.
• Comparative pharmacology: Benchmarking potency/efficacy versus other prostanoid analogs (e.g., PGE, PGF series) to dissect receptor selectivity and signaling bias.
• Chemical biology: Tool compound for evaluating IP receptor coupling to Gs-mediated cAMP signaling and downstream kinase pathways; useful in validating on-target effects in cell lines engineered to express PTGIR.
• Analytical method development: System-suitability or standard material in LC–UV/LC–MS methods for prostanoid-class analytes.

Practical handling tips:

• Prepare concentrated, light-protected stock solutions (e.g., in DMSO or ethanol) and aliquot to avoid freeze–thaw.
• Pre-equilibrate plastic consumables with buffer containing carrier protein or surfactant when working at low concentrations to reduce adsorption losses.
• Include vehicle controls to account for solvent effects in functional assays.

Reaction Conditions

This product is not intended as a reagent for routine synthetic reactions; however, the following general/literature conditions are relevant for derivatization and analytical workflows involving prostacyclin analogs like iloprost.

• Esterification (for prodrugs or analytical derivatives):

  • Conditions: Mild Steglich esterification (EDC·HCl or DCC with DMAP) in dry CH2Cl2 or DMF at 0–25°C, protected from light and oxygen.
  • Notes: Monitor for olefin isomerization; avoid strong acid/base and elevated temperatures.

• Amide coupling (bioconjugation or probe synthesis):

  • Conditions: HATU or EDC/NHS in DMF or NMP with DIPEA at 0–25°C; short reaction times (0.5–4 h) typically sufficient.
  • Notes: Use inert atmosphere; quench and purify rapidly to minimize degradation.

• Analytical method conditions (LC–MS, literature examples):

  • Reverse-phase LC with C18 columns; aqueous buffer (e.g., ammonium formate or acetate, pH ~3–5) and acetonitrile or methanol gradients; UV detection in the 195–210 nm range or MS in negative ESI due to carboxylate.
  • Sample prep: Stocks in DMSO/EtOH; dilute into mobile phase shortly before injection.

• Stability handling:

  • Work under subdued light; use amber glassware.
  • Maintain low temperature during workup/purification; store intermediates and final material at ≤−20°C, preferably −80°C (see Storage tab for this item’s storage requirement).

Safety and Handling

Hazard classification data are not provided for this specific item.

• GHS classification: Not specified for this item; refer to SDS.
• Signal word / H-statements / pictograms: Not specified for this item; refer to SDS.

General laboratory safety guidance for small-molecule prostanoid analogs (informational only):

• Potency/biological activity: Iloprost is a potent research ligand; avoid inhalation, ingestion, and skin contact. Handle solutions in a fume hood and wear appropriate PPE (lab coat, nitrile gloves, splash goggles).
• Light and air sensitivity: Protect from light and minimize air exposure to reduce degradation; use amber vials and inert gas backfill where practical.
• Incompatibilities: Avoid strong oxidizers and strong bases/acids during storage and routine handling; hydrolysis and oxidation can occur under harsh conditions.
• First aid overview: In case of skin/eye contact, rinse with water for at least 15 minutes; if inhaled, move to fresh air; if swallowed, rinse mouth. Seek medical attention in all exposure cases. Defer to the SDS for authoritative instructions.
• Waste: Dispose of solutions and contaminated materials as halogen-free organic waste or according to your institution’s policy for bioactive organics.

Always consult the SDS for SKU I1499272 for definitive hazard, handling, and first-aid guidance.

Solvent Selection

Iloprost is an amphiphilic, largely lipophilic carboxylic acid analog. Solvent choice strongly affects recovery, stability, and assay performance.

General/literature guidance (not item specifications):

• Preferred stock solvents: DMSO (anhydrous) or ethanol due to good solubility and compatibility with biological assays at low final percentages.
• Co-solvent systems: For aqueous work, dilute DMSO or ethanol stocks into buffer with vigorous mixing; keep final organic content low (≤0.1–1% v/v, as assay allows). Consider nonionic surfactants (e.g., 0.01–0.05% polysorbate 80) or cyclodextrins to reduce precipitation and adsorption.
• pH control: Solubility improves above the carboxylate pKa; brief dissolution in basic aqueous media (e.g., minimal NaOH) followed by pH readjustment may be employed when compatible with the assay.
• Container choice: Use glass or low-bind polypropylene to minimize adsorption losses at nanomolar–micromolar concentrations.

Comparison notes (literature-based):

• DMSO: Highest solvating power; may impact some targets at >0.5–1% v/v. Low volatility; hygroscopic.
• Ethanol: Lower solvating power than DMSO but broadly tolerated; more volatile; can facilitate rapid drying for coating applications.
• Aqueous buffer alone: Often insufficient unless pH-adjusted or aided by solubilizers.

Tip: Filter stocks through PTFE (if needed) rather than nylon to avoid adsorption of lipophilic acids.

Storage and Reconstitution

Storage conditions (from Product Data):

• Store at −80°C.
• Shipped with dry ice packs + cold packs.

Item-specific stabilizers, salt form, and appearance: Not specified for this item; refer to CoA/Spec Sheet.

General reconstitution and handling guidance for prostanoid analogs (not item specifications):

• Reconstitution: Dissolve promptly upon receipt in a minimal volume of anhydrous DMSO or ethanol to prepare a concentrated stock (e.g., 1–10 mM). Mix gently to avoid foaming. Protect from light (amber vials) and, if feasible, blanket headspace with inert gas.
• Aliquoting: Dispense single-use aliquots into low-bind microtubes or plates to avoid multiple freeze–thaw cycles.
• Short-term storage: Keep thawed working solutions on ice and protected from light; use within the same day for best consistency.
• Long-term storage: Maintain frozen stocks at −80°C. Avoid frost-free freezers. Document the number of freeze–thaw events; discard aliquots after a set number of uses.
• Adsorption mitigation: When preparing low-nanomolar solutions, pre-rinse plastics with buffer containing carrier protein (e.g., fatty acid–free BSA) or a trace nonionic surfactant to reduce surface binding.

Always consult the item’s CoA/Spec Sheet and SDS for authoritative instructions and stability information specific to SKU I1499272.

Structure and Identity

Iloprost is a synthetic prostacyclin (PGI2) analog used widely as a small-molecule research ligand in GPCR signaling and vascular biology studies.

• SKU: I1499272
• Product name: Iloprost
• CAS: 78919-13-8 (literature identifier)
• PubChem CID: 5311181 (literature identifier)
• InChIKey: Not specified for this item; refer to CoA/Spec Sheet.
• SMILES: Not specified for this item; refer to CoA/Spec Sheet.
• Molecular formula: Not specified for this item; refer to CoA/Spec Sheet.
• Molecular weight: Not specified for this item; refer to CoA/Spec Sheet.

Structural features (general/literature description):

• Prostanoid framework with a substituted cyclopentane core and two oxygenated side chains.
• Contains a terminal carboxylic acid, secondary alcohol functionality, and multiple olefinic segments with defined geometries in the native scaffold.
• Multiple stereocenters typical of prostanoid analogs; commercial materials may be supplied as a defined isomer or a mixture of diastereomers depending on specification (not specified for this item).
• Overall amphiphilic character: lipophilic hydrocarbon chains plus polar acid/alcohol groups.

2D structure (verbal):

• A cyclopentane ring bearing an oxygenated “upper” side chain terminating in a carboxylic acid and a more lipophilic “lower” side chain with unsaturation; at least one secondary alcohol is present on the ring or side chain, consistent with prostacyclin analog motifs.

Synthetic Utility

As a complex, functionalized prostacyclin analog, iloprost is typically the target of synthesis, not a general-purpose building block.

Utility in synthesis research (general/literature perspective):

• Total synthesis studies: Iloprost’s densely functionalized cyclopentane core with defined stereochemistry, conjugated alkene segments, secondary alcohol(s), and a terminal carboxylic acid provides a platform for testing asymmetric synthesis, protecting-group strategies, and fragment coupling.
• Derivatization: The carboxylic acid can be converted to esters or amides to modulate lipophilicity, permeability, or enable immobilization on solid supports for affinity studies. Secondary alcohol(s) allow carbonate/ether formation for prodrug or probe synthesis.
• Conjugation chemistry: Carbodiimide (EDC/NHS) or HATU-mediated coupling enables attachment to amines on reporter molecules, linkers, or surfaces; care is needed to preserve olefin geometry and avoid undesired isomerization/oxidation.

Caveats:

• The molecule’s multiple stereocenters and unsaturations are susceptible to isomerization under acid/base or light; adopt mild conditions and protect from light and oxygen during transformations.
• For SAR work, parallel synthesis of side-chain variants or ester prodrugs can be informative; verify configuration and purity rigorously by chiral/2D NMR and LC–MS.

Target Specificity

Item-specific target data are not provided in the Product Data for SKU I1499272.

• Antigen/target name, species reactivity, clone/isotype: Not applicable to this small-molecule product.

General/literature background (for experimental planning only):

• Primary pharmacological target studied with iloprost is the human prostacyclin receptor (IP; gene PTGIR). Selectivity vs other prostanoid receptors (EP/DP/FP/TP) is context-dependent and should be empirically confirmed for each assay system.

For validated, item-specific target engagement data (e.g., EC50/Ki in defined systems), consult the product’s CoA/Spec Sheet or generate in-house under your assay conditions.